Methyl iodide → HCID 58542052, compound

HRID 1966768Notes

Reaction equation

HRID 1966768 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:19]=[C:18]([CH3:20])[NH:17][N:16]=3)=[N:8][C:4]=2[CH:3]=1.CI.[C:29]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]([C:21]([CH3:23])([CH3:22])[CH3:24])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:19]=[C:18]([CH3:20])[N:17]([CH3:29])[N:16]=3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58542054HCID 58542054, compound

Product 1

HCID 58542052HCID 58542052, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a vial is added 5-bromo-1-tert-butyl-2-[2-(5-methyl-1H-[1,2,4]triazol-3-yl)-phenyl]-1H-benzimidazole (73 mg, 0.178 mmol) in DMF (1.5 mL), followed by the addition of MeI (40 mg, 0.282 mmol) and K2CO3 (49 mg, 0.355 mmol). The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with EtOAc (20 mL), washed with water, brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 0-3% 7M NH3 in MeOH/CH2Cl2 as the eluent to afford 5-bromo-1-tert-butyl-2-[2-(1,5-dimethyl-1H-[1,2,4]triazol-3-yl)-phenyl]-1H-benzimidazole (44 mg, 58%) as an off-white solid. LCMS (ESMS): m/z 424.58, 426.51 (M++1).

Workup

  1. washwashed with water, brine
  2. customdried under anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel flash column chromatography with 0-3% 7M NH3 in MeOH/CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-de2f38556800421ea1ba929823f01b60
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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